Chlorosuccinimide → HCID 178517530, compound

HRID 1484889Notes

Reaction equation

HRID 1484889 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10]([OH:12])[CH:9]=[CH:8][N:7]=1.C1C(=O)N([Cl:20])C(=O)C1>CC(O)=O>[Cl:20][C:9]1[C:10]([OH:12])=[N:11][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178516490HCID 178516490, compound

Product 1

HCID 178517530HCID 178517530, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 2-(thiophen-2-yl)pyrimidin-4-ol (100 mg, 0.56 mmol) in HOAc (3 mL) was added NCS (90 mg, 0.67 mmol, 1.2 equiv.) portionwise. The reaction mixture was stirred at 60° C. for 4 h and partitioned between brine and ethylacetate. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to give 5-chloro-2-(thiophen-2-yl)pyrimidin-4-ol (90 mg, 75%). LC-MS (m/z)=213.0 [M+H]+.

Workup

  1. custompartitioned between brine and ethylacetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-99cbea5259a54e1485760d638a0ede8c
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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